Which of the following reactions is expected to given a fairly good yield of `(CH_(3))_(3)C CH=CH_(2)`?

Options

A. `CH_(3)underset(CH_(3))underset(|)overset(CH_(3))overset(|)C-underset(Br)underset(|)(CH)CH_(3)undersetunderset(Heat)("Acetone")overset(zn)(rarr)`
B.
C. `CH_(3)underset(CH_(3))underset(|)overset(CH_(3))overset(|)C-underset(OH)underset(|)CHCH_(3)overset(H_(2)SO_(4))underset(Heat)to`
D. `CH_(3)underset(CH_(3))underset(|)overset(CH_(3))overset(|)C-underset(Br)underset(|)CHCH_(3)underset(Heat)overset((CH_(3))_(3)CO^(-)K+)to`

Answer

D

Explanation

Reaction `(1)` is not possible because `Zn//"acetone"` causes dehalogenation of dihalides. Reaction `(2)` leads to the formation of ethylene in accordance with Hofmann's rule. Reaction `(3)` leads to the formation of rearranged product `(CH_(3))_(2)=C(CH_(3))_(2)`. In reaction `(4)`, the bulky base `(CH_(3))_(3)C CH=CH_(2)`.